Jack is a fluid crossdresser who is totally into prostate play and he called in to talk all about it. Tune in to hear him discuss all the details including how and when he realized he was into wearing female clothing and what he enjoyed about it at first, when he got into trans porn and exploring anal play, his first hook-up he had with another crossdresser and exactly what went down, his stash he was accumulating and where he gets everything from, how he told one of his girlfriends that he was into pegging and how she reacted, the first guy he hooked up with and exactly what went down between them, how he brought up his crossdressing and his interest in guys to his last girlfriend and how she reacted and what followed including him getting pegged by her while he is dressed, how and why they broke up and how she threw his fetish in his face at the end, the prostate orgasms he has had and how they feel, the anal toys he enjoys the most and the ones he recommends to start out with, how he got a throat infection from deep throating a toy one time and how long it lasted plus a whole lot more.

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1154 - FETISH FRIDAY: Jack is a Fluid Crossdresser who is Totally Into Prostate Play